Fungicide Active Substance Combinations

ABSTRACT

The novel active compound combinations comprising 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thione of the formula 
     
       
         
         
             
             
         
       
     
     and the active compound of groups (1) to (24) listed in the description have very good fungicidal properties.

The present invention relates to novel active compound combinationswhich consist of the known2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thioneand further known fungicidally active compounds, and which are highlysuitable for controlling phytopathogenic fungi.

It is already known that2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thionehas fungicidal properties (cf. WO 96-16 048). The activity of thiscompound is good, however, at low application rates it is in some casesnot satisfactory.

Furthermore, it is already known that a large number of triazolederivatives, aniline derivatives, dicarboximides and other heterocyclescan be employed for controlling fungi (cf. EP-A 0 040 345, DE-A 2 201063, DE-A 2 324 0 10, Pesticide Manual, 9th Edition (1991), pages 249and 827, U.S. Pat. No. 3,903,090 and EP-A 0 206 999). Likewise, theactivity of these compounds is not always satisfactory at lossapplication rates.

Finally, it is also known that1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine can beused for controlling animal pests such as insects (cf. Pesticide Manual,9th Edition (1991), page 491). However, fungicidal properties have nothitherto been described for this compound.

It has now been found that the novel active compound combinationscomprising2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thioneof the formula

and(1) a triazole derivative of the formula

in which

-   -   X represents chlorine or phenyl    -   and    -   Y represents

and/or(2) the triazole derivative of the formula

and/or(3) an aniline derivative of the formula

in which

-   -   R¹ represents hydrogen or methyl,        and/or        (4)        N-[1-(4-chloro-phenyl)-ethyl]-2,2-dichloro-1-ethyl-3-methyl-cyclopropanecarboxamide        of the formula

and/or(5) the zinc propylene-1,2-bis-(dithiocarbamate) of the formula

-   -   n>=1        and/or        (6) at least one thiocarbamate of the formula

-   -   Me═Zn or Mn or a mixture of Zn and Mn        and/or        (7) the aniline derivative of the formula

and/or(8) the compound of the formula

and/or(9) the benzothiadiazole derivative of the formula

and/or(10) the8-t-butyl-2-(N-ethyl-N-n-propyl-amino)-methyl-1,4-dioxaspiro-[5,4]-decaneof the formula

and/or(11) the compound of the formula

and/or(12) the compound of the formula

and/or(13) the compound of the formula

and/or(14) the dicarboximide of the formula

and/or(15) a pyrimidine derivative of the formula

in which

-   -   R² represents methyl or cyclopropyl,        and/or        (16) the phenyl derivative of the formula

and/or(17) the morpholine derivative of the formula

and/or(18) the phthalimide derivative of the formula

and/or(19) the phosphorus compound of the formula

and/or(20) a phenylpyrrole derivative of the formula

in which

-   -   R³ and R⁴ each represent chlorine or together represent a        radical of the formula —O—CF₂—O—,        and/or        (21) the        1-[(6-chloro-3-pyridinyl)-methyl]-N-nitro-2-imidazolidineimine        of the formula

and/or(22) the phenylurea derivative of the formula

and/or(23) the benzamide derivative of the formula

and/or(24) a guanidine derivative of the formula

in which

-   -   m represents integers from 0 to 5    -   and    -   R⁵ represents hydrogen (17 to 23%) or the radical of the formula

have very good fungicidal properties.

Surprisingly, the fungicidal activity of the active compoundcombinations according to the invention is considerably higher than thesum of the activities of the individual active compounds. Thus, anunforeseeable, true synergistic effect is present, and not just anaddition of activities.

The2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro-[1,2,4]-triazole-3-thioneof the formula (I) is known (cf. WO 96-16 048). The compound can bepresent in the “thiono” form of the formula

or in the tautomeric “mercapto” form of the formula

For simplicity's sake, only the “thiono” form is given in each case.

The formula (II) includes the compounds1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butane-2-one ofthe formula

1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol ofthe formula

and 1-(4-phenyl-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-olof the formula

The formula (IV) includes the aniline derivatives of the formulae

It is evident from the formula for the active compound of the formula(V) that the compound has three asymmetrically substituted carbon atoms.The product may therefore be present as a mixture of various isomers, orelse in the form of a single component. Particular preference is givento the compoundsN—(R)-[1-(4-chloro-phenyl)-ethyl]-(1S)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamideof the formula

andN—(R)-[1-(4-chloro-phenyl)-ethyl]-(1R)-2,2-dichloro-1-ethyl-3t-methyl-1r-cyclopropanecarboxamideof the formula

The formula (VII) includes the compounds

Me═Zn (zineb)  (VIIa)

Me═Mn (maneb)  (VIIb)

and

mixture of (VIIa) and (VIIb) (mancozeb).  (VIII)

The formula (XVI) includes the compounds

R²═CH₃ (pyrimethanil)  (XVIa)

and

The formula (XXI) includes the compounds4-(2,3-dichlorophenyl)-pyrrole-3-carbonitrile of the formula

and 4-(2,2-difluoro-1,3-benzodioxol-7-yl)-1H-pyrrole-3-carbonitrile ofthe formula

The guanidine derivative of the formula (XXV) is a mixture of substancesof the common name guazatine.

The components which are present in the active compound combinationsaccording to the invention in addition to the active compound of theformula (I) are also known. Specifically, the active compounds aredescribed in the following publications:

(1) Compounds of the formula (II)

-   -   DE-A 2 201 063    -   DE-A 2 324 010        (2) Compound of the formula (III)    -   EP-A 0 040 345        (3) Compounds of the formula (IV)    -   Pesticide Manual, 9th Edition (1991), pages 249 and 827        (4) Compound of the formula (V) and individual isomers thereof    -   EP-A 0 341 475        (5) Compound of the formula (VI)    -   Pesticide Manual, 9th Edition (1991), page 726        (6) Compounds of the formula (VII)    -   Pesticide Manual, 9th Edition (1991), pages 529, 531 and 866        (7) Compound of the formula (VIII)    -   EP-A 0 339 418        (8) Compound of the formula (IX)    -   EP-A 0 472 996        (9) Compound of the formula (X)    -   EP-A 0 313 512        (10) Compound of the formula (XI)    -   EP-A 0 281 842        (11) Compound of the formula (XII)    -   EP-A 0 382 375        (12) Compound of the formula (XIII)    -   EP-A 0 515 901        (13) Compound of the formula (XIV)    -   EP-A 196 02 095        (14) Compound of the formula (XV)    -   US-A 3 903 090        (15) Compounds of the formula (XVI)    -   EP-A 0 270 111    -   EP-A 0 310 550        (16) Compound of the formula (XVII)    -   Pesticide Manual, 9th Edition (1991), page 159        (17) Compound of the formula (XVIII)    -   EP-A 0 219 756        (18) Compound of the formula (XIX)    -   Pesticide Manual, 9th Edition (1991), page 431        (19) Compound of the formula (XX)    -   Pesticide Manual, 9th Edition (1991), page 443        (20) Compounds of the formula (XXI)    -   EP-A 0 236 272    -   EP-A 0 206 999        (21) Compound of the formula (XXII)    -   Pesticide Manual, 9th Edition (1991), page 491        (22) Compound of the formula (XXIII)    -   DE-A 2 732 257        (23) Compound of the formula (XXIV)    -   EP-A 0 600 629        (24) Substance of the formula (XXV)    -   Pesticide Manual, 9th Edition (1991), page 461

In addition to the active compound of the formula (I), the activecompound combinations according to the invention comprise at least oneactive compound of the compounds of groups (1) to (24). Additionally,they may comprise further fungicidally active components.

The synergistic effect is particularly pronounced when the activecompounds in the active compound combinations according to the inventionare present in certain weight ratios. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range. In general,

0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, ofactive compound of group (1),0.1 to 20 parts by weight, preferably 0.2 to 10 parts by weight, ofactive compound of group (2),0.2 to 150 parts by weight, preferably 1 to 100 parts by weight, ofactive compound of group (3),0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, ofactive compound of group (4),1 to 50 parts by weight, preferably 5 to 20 parts by weight, of activecompound of group (5),1 to 50 parts by weight, preferably 2 to 20 parts by weight, of activecompound of group (6),0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of activecompound of group (7),0.2 to 50 parts by weight, preferably 1 to 20 parts by weight, of activecompound of group (8),0.02 to 50 parts by weight, preferably 0.2 to 10 parts by weight, ofactive compound of group (9),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, ofactive compound of group (10),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, ofactive compound of group (11),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, ofactive compound of group (12),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, ofactive compound of group (13),0.1 to 50 parts by weight, preferably 1 to 30 parts by weight, of activecompound of group (14),0.1 to 50 parts by weight, preferably 0.2 to 20 parts by weight, ofactive compound of group (15),0.1 to 50 parts by weight, preferably 2 to 20 parts by weight, of activecompound of group (16),1 to 20 parts by weight, preferably 2 to 10 parts by weight, of activecompound of group (17),1 to 50 parts by weight, preferably 2 to 20 parts by weight, of activecompound of group (18),1 to 50 parts by weight, preferably 2 to 20 parts by weight, of activecompound of group (19),0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, ofactive compound of group (20),0.05 to 20 parts by weight, preferably 0.1 to 10 parts by weight, ofactive compound of group (21),0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, ofactive compound of group (22),0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, ofactive compound of group (23),and/or0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, ofactive compound of group (24)are present per part by weight of active compound of the formula (I).

The active compound combinations according to the invention have verygood fungicidal properties and can be employed for controllingphytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes,Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes,Deuteromycetes, etc.

The active compound combinations according to the invention areparticularly suitable for controlling cereal diseases, such as Erysiphe,Puccinia and Fusarium, and for controlling diseases encountered inviticulture, such as Uncinula, Plasmopara and Botrytis, and furthermorein dicotyledonous crops for controlling powdery and downy mildew fungiand causative organisms of leaf spot.

The fact that the active compound combinations are well tolerated byplants at the concentrations required for controlling plant diseasespermits the treatment of above-ground parts of plants, of propagationstock and seeds, and of the soil. The active compound combinationsaccording to the invention can be employed for foliar application orelse as seed dressings.

The active compound combinations according to the invention can beconverted to the customary formulations, such as solutions, emulsions,suspensions, powders, foams, pastes, granules, aerosols andmicroencapsulations in polymeric substances and in coating compositionsfor seeds, and ULV formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds or active compound combinations with extenders,that is liquid solvents, liquefied gases under pressure, and/or solidcarriers, optionally with the use of surfactants, that is emulsifiersand/or dispersants, and/or foam formers. If the extender used is water,it is also possible to use, for example, organic solvents as auxiliarysolvents. Essentially, suitable liquid solvents include: aromatics suchas xylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water. Liquefied gaseous extenders or carriers areto be understood as meaning liquids which are gaseous at ambienttemperature and under atmospheric pressure, for example aerosolpropellants such as butane, propane, nitrogen and carbon dioxide.Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkyl-sulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignin-sulphitewaste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and prussian blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compounds, preferably between 0.5 and 90%.

In the formulations, the active compound combinations according to theinvention can be present as a mixture with other known active compoundssuch as fungicides, insecticides, acaricides and herbicides, and asmixtures with fertilizers or plant growth regulators.

The active compound combinations can be used as such, in the form oftheir formulations or as the use forms prepared therefrom, such asready-to-use solutions, emulsifiable concentrates, emulsions,suspensions, wettable powders, soluble powders and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, spreading, and as a powder for dry seedtreatment, a solution for seed treatment, a water-soluble powder forseed treatment, a water-soluble powder for slurry treatment, or byencrusting.

When using the active compound combinations according to the invention,the application rates can be varied within a relatively wide range,depending on the kind of application. In the treatment of parts ofplants, the application rates of the active compound combination aregenerally between 0.1 and 10,000 g/ha, preferably between 10 and 1000g/ha. In the treatment of seeds, the application rates of the activecompound combination are generally between 0.001 and 50 g per kilogramof seed, preferably between 0.01 and 10 g per kilogram of seed. In thetreatment of the soil, the application rates of the active compoundcombination are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

The good fungicidal activity of the active compound combinationsaccording to the invention is evident from the examples below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually.

The expected activity for a given combination of two active compoundscan be calculated as follows (cf. Colby, S. R., “Calculating Synergisticand Antagonistic Responses of Herbicide Combinations”, Weeds 15, (1967),20-22).

If

-   -   X is the efficacy when applying active compound A at an        application rate of m g/ha,    -   Y is the efficacy when applying active compound B at an        application rate of n g/ha and    -   E is the efficacy when applying the active compounds A and B at        an application rate of m and n g/ha,        then

$E = {X + Y - \frac{X \cdot Y}{100}}$

The efficacy is calculated in %. 0% is an efficacy which corresponds tothat of the control, whereas an efficacy of 100% means that no infectionis observed.

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

The examples that follow illustrate the invention.

EXAMPLE 1 Sphaerotheca Test (Cucumber)/Protective

-   -   Solvent: 47 parts by weight of acetone    -   Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 1 Sphaerotheca test (cucumber)/protective Active compound Activecompound Known: application rate in g/ha Efficacy in %

  (I) 2.5 0.5 21  0

  (VI) 25    0

  (IVa) 25    0

  (IVb) 25    0

  (VIIc) 25    0

  (XIX) 25    0

  (XX) 50    0

  (XVII) 25    0

  (XVIa) 25    0

  (XVIb) 25    0

  (XXIV) 12.5   0

  (XVIII) 12.5   0

  (XV) 12.5   0

  (VIII) 12.5   0

  (XI) 12.5   0

  (XIII) 2.5 57

  (XII) 2.5 59

  (IX) 12.5  13

  (IIc) 2.5  0

  (III) 2.5 50

  (IIa) 2.5 37

  (IIb) 2.5 80

  (XIV) 2.5 22

  (X) 2.5  0 Active compound Active compound Efficacy in % According tothe invention: application rate in g/ha found calc *)

  (1:10)

70 21

  (1:10)

63 21

  (1:10)

63 21

  (1:10)

63 21

  (1:10)

59 21

  (1:20)

52 21

  (1:10)

63 21

  (1:10)

59 21

  (1:10)

52 21

  (1:5)

50 21

  (1:5)

63 21

  (1:5)

50 21

  (1:5)

75 21

  (1:5)

54 21

  (1:5)

80 57

  (1:5)

75 59

  (1:5)

66 31

  (1:1)

90 21

  (1:1)

85 61

  (1:1)

90 50

  (1:1)

93 84

  (1:1)

70 38

  (1:1)

52 21 found = efficacy found calc. = efficacy calculated using the Colbyformula

EXAMPLE 2 Venturia Test (Apple)/Protective

-   -   Solvent: 47 parts by weight of acetone    -   Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueouskonidia suspension of the causative organism of apple scab Venturiainaequalis and then remain in an incubation cabin at about 20° C. and100% relative atmospheric humidity for one day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 2 Venturia test (apple)/protective Active compound Active compoundKnown: application rate in g/ha Efficacy in %

  (I) 1 1

  (1:1 mixture) 1 0 Active compound Active compound Efficacy in %According to the invention: application rate in g/ha found calc *)

  (1:1)

54 1 found = efficacy found calc. = efficacy calculated using the Colbyformula

EXAMPLE 3 Erysiphe Test (Barley)/Curative

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f. sp. hordei. 48 hours after the inoculation, theplants are sprayed with the active compound preparation at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 3 Erysiphe test (barley)/curative Active compound Active compoundapplication rate in g/ha Efficacy in % Known:

  (I) 25 81

  (XIV) 25 75 According to the invention:

  (1:3)

100

EXAMPLE 4 Erysiphe Test (Barley)/Protective

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f. sp. hordei.

The plants are placed in a greenhouse at a temperature of about 20° C.and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below

TABLE 4 Erysiphe test (barley)/curative Active compound Active compoundapplication rate in g/ha Efficacy in % Known:

  (I) 25 83

  (XII) 25 92 According to the invention:

  (1:1)

100

  (1:3)

100

  (3:1)

100

EXAMPLE 5 Erysiphe Test (Wheat)/Curative

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f. sp. tritici. 48 hours after the inoculation, theplants are sprayed with the active compound preparation at the statedapplication rate.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 5 Erysiphe test (wheat)/curative Active compound Active compoundapplication rate in g/ha Efficacy in % Known:

  (I) 25   12.5   6.25  75  50  25

  (III) 25    88

  (IIb) 25    81

  (XIV) 12.5   0

  (XI) 12.5   0

  (XVIb) 12.5   0

 (XXIb)  6.25  38

  (XIII)  6.25  94 According to the invention:

  (1:1)

100

  (1:3)

100

  (3:1)

100

  (1:1)

100

  (1:3)

100

  (1:1)

 63

  (3:1)

 75

  (1:1)

100

  (1:3)

100

  (3:1)

100

  (1:1)

 75

  (1:3)

 50

  (1:1)

100

  (1:3)

100

EXAMPLE 6 Erysiphe Test (Wheat)/Protective

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f. sp. tritici.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80% to promote thedevelopment of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 6 Erysiphe test (wheat)/protective Active compound Active compoundapplication rate in g/ha Efficacy in % Known:

  (I) 6.25 57

  (III) 6.25 57 According to the invention:

  (1:1)

79

  (1:3)

71

  (3:1)

71

EXAMPLE 7 Leptosphaeria nodorum Test (Wheat)/Protective

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are sprayed with theactive compound preparation at the stated application rate.

After the spray coating has dried on, the plants are sprayed with aspore suspension of Leptosphaeria nodorum. The plants remain in anincubation cabin at 20° C. and 100% relative atmospheric humidity for 48hours.

The plants are then placed in a greenhouse at a temperature of about 15°C. and a relative atmospheric humidity of about 80%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 7 Leptosphaeria nodorum test (wheat)/protective Active compoundActive compound application rate in g/ha Efficacy in % Known:

  (I) 25 62

  (XIV) 25 87 According to the invention:

  (1:3)

100

EXAMPLE 8 Puccinia Test (Wheat)/Protective

-   -   Solvent: 10 parts by weight of N-methyl-pyrrolidone    -   Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration, or a commercial formulation ofactive compound or active compound combination is diluted with water tothe desired concentration.

To test for protective activity, young plants are inoculated with aspore suspension of Puccinia recondita in a 0.1% strength aqueous agarsolution. After the spray coating had dried on, the plants are sprayedwith the active compound preparation at the stated application rate.

The plants remain in an incubation cabin at 20° C. and 100% relativeatmospheric humidity for 24 hours.

The plants are then placed in a greenhouse at a temperature of about 20°C. and a relative atmospheric humidity of about 80% to promote thedevelopment of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 8 Puccinia test (wheat)/protective Active compound Active compoundapplication rate in g/ha Efficacy in % Known:

  (I) 25 38

  (XIV) 25 94 According to the invention:

  (1:3)

100

  (3:1)

100

EXAMPLE 9 Fusarium culmorum Test (Wheat)/Seed Treatment

The active compounds are applied as a dry seed dressing. This isprepared by extending the respective active compound or the activecompound combination with ground minerals to give a finely pulverulentmixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing isshaken for 3 minutes in a sealed glass flask.

2×100 corns of wheat are sown at a depth of 1 cm in standard soil andcultivated in a greenhouse at a temperature of about 18° C. and arelative atmospheric humidity of about 95% in seed trays which receive alight regimen of 15 hours per day.

About 3 weeks after sowing, the plants are evaluated for symptoms. 0%means an efficacy which corresponds to that of the control, whereas anefficacy of 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE 9 Fusarium culmorum test (wheat)/seed treatment Active compoundActive compound application rate in g/ha Efficacy in % Known:

  (I) 75 32

  (IIc) 75 27 According to the invention:

  (1:1)

41

EXAMPLE 10 Fusarium nivale Test (Triticale)/Seed Treatment

The active compounds are applied as a dry seed dressing. This isprepared by extending the respective active compound or the activecompound combination with ground minerals to give a finely pulverulentmixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing isshaken for 3 minutes in a sealed glass flask.

2×100 corns of wheat are sown at a depth of 1 cm in standard soil andcultivated in a greenhouse at a temperature of about 10° C. and arelative atmospheric humidity of about 95% in seed trays which receive alight regimen of 15 hours per day.

About 3 weeks after sowing, the plants are evaluated for symptoms. 0%means an efficacy which corresponds to that of the control, whereas anefficacy of 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below

TABLE 10 Fusarium nivale test (triticale)/seed treatment Active compoundActive compound application rate in g/ha Efficacy in % Known:

  (I) 75 25 14  0

  (XIV) 75 94

  (XXIa) 25  0 According to the invention:

  (1:1)

99

  (1:1)

31

EXAMPLE 11 Rhizoctonia solani Test (Cotton)/Seed Treatment

The active compounds are applied as a dry seed dressing. This isprepared by extending the respective active compound or the activecompound combination with ground minerals to give a finely pulverulentmixture which ensures uniform distribution on the seed surface.

To dress the seed, the infected seed together with the seed dressing isshaken for 3 minutes in a sealed glass flask.

2×50 corns of seed are sown at a depth of 2 cm in standard soil infectedwith Rhizoctonia solani, and the seeds are cultivated in a greenhouse ata temperature of about 22° C. in seed trays which receive a lightregimen of 15 hours per day.

Evaluation is carried out after 8 days. 0% means an efficacy whichcorresponds to that of the control, whereas an efficacy of 100% meansthat no infection is observed.

Active compounds, application rates and test results are shown in thetable below

TABLE 11 Rhizoctonia solani test (cotton)/seed treatment Active compoundActive compound application rate in g/ha Efficacy in % Known:

  (I) 25 19

  (III) 25 27

  (IIc) 25 0 According to the invention:

  (1:1)

40

  (1:1)

31

1.-5. (canceled)
 6. A fungicidal composition comprising synergisticallyeffective amounts of: (a) a2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thioneof the formula

and (b) a triazole derivative of the formula

wherein the weight ratio of active compound of the formula (I) to theactive compound of the formula (III) is from 1:0.2 to 1:10.
 7. Thecomposition of claim 6 wherein the weight ratio of the active compoundof formula (I) to the compound of formula (III) is from 1:0.33 to 1:3.8. A method for controlling fungi comprising applying the compositionaccording to claim 6 or 7 to the fungi and/or their habitat.
 9. Afungicidal composition comprising synergistically effective amounts of:(a) a2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thioneof the formula

and (b) a triazole derivative of the formula

wherein the weight ratio of active compound of the formula (I) to theactive compound of the formula (III) is from 1:1 to 1:3.
 10. A methodfor controlling fungi comprising applying the composition according toclaim 9 to the fungi and/or their habitat.
 11. The method according toclaim 10 wherein the fungi is a cereal disease.
 12. The method accordingto claim 11 wherein the cereal disease is selected from the groupconsisting of Erysiphe, Puccinia, and Fusarium.
 13. The method accordingto claim 10 wherein the composition is applied to plant parts at a ratebetween 10 and 1000 g/ha.
 14. The method according to claim 10 whereinthe composition is applied to soil at a rate between 1 and 5000 g/ha.15. A method for controlling fungi comprising applying a fungicidalcomposition comprising: (a) a2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]2,4-dihydro-[1,2,4]-triazole-3-thioneof the formula

and (b) a triazole derivative of the formula

wherein the weight ratio of active compound of the formula (I) to theactive compound of the formula (III) is from 1:0.2 to 1:10.
 16. Themethod according to claim 15 wherein the weight ratio of active compoundof the formula (I) to the active compound of the formula (III) is from1:0.33 to 1:3.
 17. The method according to claim 15 wherein the weightratio of active compound of the formula (I) to the active compound ofthe formula (III) is from 1:1 to 1:3.
 18. The method according to claim15 wherein the fungi is a cereal disease.
 19. The method according toclaim 18 wherein the cereal disease is selected from the groupconsisting of Erysiphe, Puccinia, and Fusarium.
 20. The method accordingto claim 15 wherein the composition is applied to plant parts at a ratebetween 10 and 1000 g/ha.
 21. The method according to claim 15 whereinthe composition is applied to soil at a rate between 1 and 5000 g/ha.22. The method according to claim 20 wherein the composition is appliedto plant parts at a rate between 25 to 1000 g/ha.